Hydrogenated polyalkylated phenol



jFalcnied June 8, i948 estates No Drag. application April 119, was,Serial We. stress 3 illaims. (59E. sees The present invention relates toa new com pound, namely 2,-i,d=tri-tertiary-butyi cyclohez anone, and toa method of preparing the same.

The primary object of the present invention is to produce the aforesaidcompound.

In accordance with our invention, a new compound, namely,2,4,6-tri-tertiary-butyl cyclohexanone, is prepared by hydrogenating2&6- tri-tertiarybutyl phenol at elevated temperatures and pressures andin the presence of a hydrogenation catalyst, until the phenol hasabsorbed atoms of combined hydrogen per molecule.

In practicing our invention, 2,4,6-trl-tertiarybutyl phenol is subjectedto the action of hy drogen at pressures of from 1600 to 2500 munds persquare inch in the presence of a relatively small amount of ahydrogenation catalyst, such as Haney or other form of nickel, platinumor palladium, and at temperatures between 160 and 250 Tl'ie operationcan be carried out either continuously or in a batch manner, the latterbeing preferred. In carrying out our process in a batch, the phenol isplaced in a suitable pressure resisting container, such as a rockingpressure bomb, in the presence of from 8 toll per cent of catalyst, andin the presence of suflicient hydrogen to maintains. pressure of 1400pounds per square inch. The bomb is then sealed and heated to an initialreaction temperature or about 175 C. or until the hydrogen pressureapproximates 2100 pounds per square inch. Heating is then continueduntil the temperature has reached approximately 230 C. and the pressurein the bomb has substantially decreased, thus indicating completion ofthe reaction. The bomb is then allowed to cool, after which its contentsare removed and filtered to separate the catalyst from the hydrogenatedproduct, which may then be further purified by rectification,sublimation or recrystallization, or other suitable method, to purify itand separate it from the initial starting material.

When the hydrogenation is carried out as aforesaid, destructivehydrogenation is avoided, the reaction being limited to absorption ofhydrogen. In other words, the hydrogenation is not carried on to yield ahydrocarbon nor are the rings opened nor any groups removed.

It will be understood that the pressure and temperature are necessarilyinterdependent to a considerable degree and that the higher theoperating pressure the lower will be the temperature required to eflecthydrogenation, within the limits stated. While the initial pressure isnot as important as the pressure dur the reaction period, it must M highenough to insure that there will be sumcient hydrogen present tocomplete the desired hydrogenation reaction, and g to provide a moderateexcess oi hydrogen over that actually absorbed in the reaction.

Example 60 parts oi 2,4,6-tri-tertiary-butyl phenol, 8 parts oi'Raneynickel catalyst, and 1360 pounds per square inch or hydrogen werecharged to a rocking bomb. The bomb was electrically heated for a periodof about four and one-half hours until a reaction temperature or about175 C. and a pressure oi about 210G pounds per square inch of hydrogenwere obtained. The reaction was completed after the heating had beencontinued for a further period of about one hour and when a temmratureof about 230 C. and a final pressure of about 2000 pounds mr square inchhad beenobtained. This pressure drop corresponded to the addition of 2mols of hydrogen at the conditions stated. After cooling the bombovernight, the contents thereof were discharged and filtered, and thehydrogenation product was a white solid. consisting of long lustrousneedles. This product, after recrystallization, had the followingproperties:

30 M. P. Per Cent 0 Percent H 0. Found 136. 8-137. 5 80. 97 Calculated81. 20

35 It is believed that the following formula illustrates the reactionproduct obtained in the above example:

on Thus we have described a new and useful compound herein specificallydescribed and a proceat for preparing it.

What we claim is: 1. As a new product, a compound having the iollowingstructural formula: 1

cnnlc-nc \CH-C(CH|)| 0 R v V 2. A method of converting2,4.6-tri-tertiarybutyl phenol into 2,4,6-trl-tertiary-butylcyclohexanone which comprises subjecting said phenol to a reactionpressure of hydrogen oi from 1600 to 2500 pounds per square inch and toa. temperature of from 160 to 250 C. in the presence of a hydrogenationcatalyst and continuing the m reaction until the addition of 4 atoms 01'hydro gen per molecule of said phenol is obtained.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Name Number Date Lazier July 20, 1937

